Rob talks startups and finance with Michael Katchen, founder of Wealthsimple, a technology platform that manages your investments. Originally published in June, 2015.

CrowdRiff by #smallrooms

Trainer+ by #smallrooms

Matt Roberts | ScaleUP Ventures by #smallrooms

Nudge Rewards Revisited by #smallrooms

Moore talks about how his past creating an unsuccessful startup and how it affects the way he approaches his current company, how he thinks about attacking an entrenched market with a variety of incumbents and new entrants, and the rationale behind taking a strategic investment from Diagram.

Rob Kenedi sits down for a coffee with Michael Kousaie, Head of Technology Business Development for the Toronto Stock Exchange and the TSX Venture Exchange. Kousaie, discusses not only the traditional path to going pubilc and how the TSX helps companies get there, but also focuses on the venture exchange as an alternate path to raising capital around the series A and B timeframe. Kenedi digs deeply into the mindset of investors on the venture exchange and their expectations, how entrepreneurs know if it is the right path for them, and how he thinks of the path to IPO with respect to the behaviour of startups in Silicon Valley and their reluctance to go public.

Nudge.ai by #smallrooms

Rob Kenedi has a coffee with Matthew Liebowitz, partner at Plaza Ventures. Matthew talks about their approach to growth investing at Series A enterprise-focused SaaS startups, the fact that the fund is always raising capital rather than in huge lump sums, the fact that the partners are compensated only on performance of the portfolio, and what failure looks like when investing into this later phase of a startup's development.

PostBeyond by #smallrooms

In this special retrospective recorded 1 year ago, Rob Kenedi speaks with Sam Molyneux, founder of Meta(at the time known as ScienceScape). Meta is a startup that uses machine learning to look at all of the journals being published in science to uncover emerging discoveries and anticipate their impact ahead of time. The Chan Zuckerberg Initiative just acquired them last week. Full disclosure: Meta is a client of TWG, where Rob Kenedi serves as Entrepreneur in Residence. Sam discusses the key use cases of Meta, why he (as a scientist) saw the need to build a company, how they think about iterating on their product, and how to build an exceptionally complex product that is net new to an industry.

Rob Kenedi chats with Hany Fahim, founder of VM Farms, a devops as a service startup, which helps companies focus on developing software rather than managing it. Fahim discusses his decision to bootstrap rather than look for external financing, how to price his product against Amazon, when to hire a sales person, and a play-by-play of how the team found product/market fit.

Host Rob Kenedi has a coffee with Nima Gardideh of Suto, an SMS-based bot that recommends the best product to buy. Gardideh has just pivoted away from this particular business and describes how it worked and why it made sense to move on. He also discusses what he had learned from Venio, an Extreme Startups cohort member and his first startup, and how to wind one down with employees and investors. Gardideh also describes being a product manager at very successful Canadian startups Frank + Oak and Taplytics, and how he applied all of those learnings to his venture while he took it through the Y Combinator Fellowship program.

Rob has a chat with Richard of Riipen, a matchmaking system for companies and students that uses experiential learning. The company was recently featured in BetaKit, but Rob had a chance to get behind the scenes with another cofounder. Richard talks about the unorthodox start to Riipen, transforming from a school project that he was advising to a fully fledged social impact-focused business. They also discuss the 10 incubators / accelerators Riipen went through, losing your tech team, and what it is like running a startup that’s distributed in nature. Disclosure: Richard is a client of TWG’s where Rob serves as Entrepreneur in Residence.

Rob Kenedi sits down with Hussein Fazal, founder SnapTravel, a SMS, Slack and Facebook Messenger bot-based hotel booking service. Hussein discusses how and when he decided to sell his last startup, AdParlor, and how he is approaching latest endeavour. In particular, he describes how to navigate a hot, new space that hasn't yet found well-understood user experience as well as the how to solve for the imperfect science of natural language processing and machine learning.

Blockthrough by #smallrooms

Medstack by #smallrooms

Collision 2016 Investors by #smallrooms

Collision 2016 Entrepreneurs by #smallrooms

Rob Kenedi a coffee with Gary Saarenvirta, founder of Daisy Intelligence, a business insights tool based on artificial intelligence. Gary discusses successfully bootstrapping his company based on his experience by first building a services company, what is not artificial intelligence, and how to rationally grow a business while competing with companies such as IBM.